NPASS Compound

Structure

NPC474370 OpenBabel07101719512D 34 39 0 0 1 0 0 0 0 0999 V2000 -7.1527 3.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7707 5.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5054 4.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4836 4.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7926 5.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 4.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8363 4.9680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5491 3.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1235 6.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1369 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4325 7.0780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 5.9190 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 5 27 1 0 0 0 0 6 7 2 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 9 1 0 0 0 0 8 17 1 0 0 0 0 9 26 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 14 2 0 0 0 0 14 25 1 0 0 0 0 15 3 1 1 0 0 0 15 24 1 0 0 0 0 16 11 1 1 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 27 1 6 0 0 0 18 26 1 6 0 0 0 19 24 1 0 0 0 0 19 29 1 6 0 0 0 20 15 1 1 0 0 0 20 33 1 0 0 0 0 21 27 1 0 0 0 0 21 30 2 0 0 0 0 22 28 1 6 0 0 0 22 31 1 0 0 0 0 23 28 1 6 0 0 0 23 34 1 0 0 0 0 24 26 1 6 0 0 0 25 32 2 0 0 0 0 25 33 1 0 0 0 0 26 4 1 6 0 0 0 27 28 1 6 0 0 0 28 34 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.27
Volume:	483.701
LogP:	3.648
LogD:	3.893
LogS:	-4.582
# Rotatable Bonds:	2
TPSA:	93.2
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	5.856
Fsp3:	0.821
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.2
MDCK Permeability:	3.258170181652531e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.672
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	75.50248718261719%
Volume Distribution (VD):	1.076
Pgp-substrate:	15.177482604980469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.627
CYP2C19-inhibitor:	0.189
CYP2C19-substrate:	0.897
CYP2C9-inhibitor:	0.261
CYP2C9-substrate:	0.027
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.072
CYP3A4-inhibitor:	0.898
CYP3A4-substrate:	0.83

ADMET: Excretion

Clearance (CL):	18.02
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.608
Human Hepatotoxicity (H-HT):	0.179
Drug-inuced Liver Injury (DILI):	0.373
AMES Toxicity:	0.085
Rat Oral Acute Toxicity:	0.313
Maximum Recommended Daily Dose:	0.594
Skin Sensitization:	0.598
Carcinogencity:	0.752
Eye Corrosion:	0.072
Eye Irritation:	0.085
Respiratory Toxicity:	0.968

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC474370

Natural Product ID:	NPC474370
*Common Name:**	SRYIGVUIFUEHSZ-LBVAZTCYSA-N
IUPAC Name:	n.a.
Synonyms:	16-Deacetyliochromolide
Standard InCHIKey:	SRYIGVUIFUEHSZ-LBVAZTCYSA-N
Standard InCHI:	InChI=1S/C28H38O6/c1-13-10-20(33-25(32)14(13)2)15(3)24-19(29)12-18-16-11-23-28(34-23)22(31)7-6-21(30)27(28,5)17(16)8-9-26(18,24)4/h6-7,15-20,22-24,29,31H,8-12H2,1-5H3/t15-,16-,17+,18+,19+,20-,22+,23-,24+,26+,27+,28-/m1/s1
SMILES:	CC1=C(C)C(=O)O[C@H](C1)[C@H]([C@H]1[C@@H](O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H]2[C@]3([C@]1(C)C(=O)C=C[C@@H]3O)O2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465677
PubChem CID:	44566999
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001560] Withanolides and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO1978	Dunalia brachyacantha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421731]
NPO1978	Dunalia brachyacantha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO1978	Dunalia brachyacantha	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	4

Activity Type	# Activity
Individual Protein	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CQ	=	0.49	uM	PMID[508247]
NPT440	Individual Protein	Quinone oxidoreductase	Mus musculus	CD	<	0.32	uM	PMID[508247]
NPT2	Others	Unspecified		Ratio	>	2.1	n.a.	PMID[508247]
NPT27	Others	Unspecified		IC50	=	660.0	nM	PMID[508247]
NPT2	Others	Unspecified		Ratio	=	1.3	n.a.	PMID[508247]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC474370 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	238
0.1-0.2	1313
0.2-0.3	3964
0.3-0.4	7650
0.4-0.5	12895
0.5-0.6	6740
0.6-0.7	6743
0.7-0.8	2827
0.8-0.85	220
0.85-0.9	53
0.9-0.95	41
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9909	High Similarity	NPC264954
0.9821	High Similarity	NPC88326
0.9821	High Similarity	NPC153700
0.9818	High Similarity	NPC50774
0.9818	High Similarity	NPC709
0.9727	High Similarity	NPC20302
0.9727	High Similarity	NPC167606
0.9727	High Similarity	NPC140055
0.9727	High Similarity	NPC286528
0.9727	High Similarity	NPC470492
0.9649	High Similarity	NPC8374
0.9558	High Similarity	NPC67569
0.955	High Similarity	NPC470493
0.955	High Similarity	NPC312824
0.955	High Similarity	NPC183580
0.9474	High Similarity	NPC470265
0.9474	High Similarity	NPC23786
0.9464	High Similarity	NPC186525
0.9455	High Similarity	NPC122056
0.9391	High Similarity	NPC469789
0.9386	High Similarity	NPC473256
0.9386	High Similarity	NPC470878
0.9381	High Similarity	NPC61520
0.9369	High Similarity	NPC147912
0.9369	High Similarity	NPC67259
0.9292	High Similarity	NPC329736
0.9231	High Similarity	NPC293112
0.9211	High Similarity	NPC473274
0.9189	High Similarity	NPC191620
0.9145	High Similarity	NPC8369
0.9145	High Similarity	NPC470494
0.9145	High Similarity	NPC172154
0.9145	High Similarity	NPC81736
0.9145	High Similarity	NPC3381
0.9115	High Similarity	NPC64318
0.9115	High Similarity	NPC270929
0.906	High Similarity	NPC11895
0.9052	High Similarity	NPC46570
0.9043	High Similarity	NPC473270
0.9035	High Similarity	NPC243065
0.9	High Similarity	NPC473593
0.8974	High Similarity	NPC269642
0.8974	High Similarity	NPC107493
0.8974	High Similarity	NPC170538
0.8929	High Similarity	NPC470961
0.8929	High Similarity	NPC474315
0.8908	High Similarity	NPC473635
0.8879	High Similarity	NPC475041
0.886	High Similarity	NPC284915
0.8852	High Similarity	NPC231240
0.885	High Similarity	NPC476163
0.8839	High Similarity	NPC29133
0.8833	High Similarity	NPC473253
0.8833	High Similarity	NPC287423
0.878	High Similarity	NPC316915
0.8739	High Similarity	NPC204812
0.8739	High Similarity	NPC91034
0.8707	High Similarity	NPC476965
0.8707	High Similarity	NPC470959
0.8689	High Similarity	NPC470880
0.8689	High Similarity	NPC231529
0.8684	High Similarity	NPC236217
0.8673	High Similarity	NPC37116
0.8667	High Similarity	NPC32868
0.8667	High Similarity	NPC241456
0.8644	High Similarity	NPC154491
0.8644	High Similarity	NPC268530
0.8644	High Similarity	NPC79579
0.8632	High Similarity	NPC153440
0.8632	High Similarity	NPC257457
0.8632	High Similarity	NPC311554
0.8621	High Similarity	NPC190286
0.8584	High Similarity	NPC475065
0.8583	High Similarity	NPC473979
0.8571	High Similarity	NPC4021
0.8571	High Similarity	NPC159456
0.8571	High Similarity	NPC329048
0.8571	High Similarity	NPC330011
0.8559	High Similarity	NPC476960
0.8559	High Similarity	NPC475520
0.8559	High Similarity	NPC473203
0.8559	High Similarity	NPC5292
0.8547	High Similarity	NPC471854
0.8537	High Similarity	NPC476966
0.8525	High Similarity	NPC156797
0.8525	High Similarity	NPC473265
0.8525	High Similarity	NPC470882
0.8522	High Similarity	NPC69291
0.8512	High Similarity	NPC469790
0.8496	Intermediate Similarity	NPC475418
0.8496	Intermediate Similarity	NPC472825
0.8496	Intermediate Similarity	NPC318363
0.8496	Intermediate Similarity	NPC473482
0.8487	Intermediate Similarity	NPC474585
0.8487	Intermediate Similarity	NPC476961
0.8487	Intermediate Similarity	NPC251226
0.848	Intermediate Similarity	NPC469673
0.8468	Intermediate Similarity	NPC220757
0.8468	Intermediate Similarity	NPC196921
0.8462	Intermediate Similarity	NPC176840
0.8462	Intermediate Similarity	NPC470075
0.8455	Intermediate Similarity	NPC473620
0.8448	Intermediate Similarity	NPC317210
0.8448	Intermediate Similarity	NPC250109
0.8443	Intermediate Similarity	NPC159499
0.8435	Intermediate Similarity	NPC470960
0.843	Intermediate Similarity	NPC120724
0.843	Intermediate Similarity	NPC6193
0.8421	Intermediate Similarity	NPC284828
0.8421	Intermediate Similarity	NPC472216
0.8421	Intermediate Similarity	NPC474901
0.8421	Intermediate Similarity	NPC173905
0.8421	Intermediate Similarity	NPC475941
0.8421	Intermediate Similarity	NPC5475
0.8413	Intermediate Similarity	NPC476823
0.8407	Intermediate Similarity	NPC473284
0.8407	Intermediate Similarity	NPC144459
0.8403	Intermediate Similarity	NPC270850
0.8403	Intermediate Similarity	NPC305260
0.8403	Intermediate Similarity	NPC42673
0.84	Intermediate Similarity	NPC34963
0.839	Intermediate Similarity	NPC469684
0.839	Intermediate Similarity	NPC239273
0.839	Intermediate Similarity	NPC185287
0.839	Intermediate Similarity	NPC55296
0.8387	Intermediate Similarity	NPC471407
0.8387	Intermediate Similarity	NPC35109
0.8362	Intermediate Similarity	NPC100267
0.8362	Intermediate Similarity	NPC475524
0.8362	Intermediate Similarity	NPC269530
0.8362	Intermediate Similarity	NPC475970
0.8348	Intermediate Similarity	NPC473627
0.8333	Intermediate Similarity	NPC58029
0.8333	Intermediate Similarity	NPC476962
0.8333	Intermediate Similarity	NPC220155
0.832	Intermediate Similarity	NPC241935
0.832	Intermediate Similarity	NPC279478
0.832	Intermediate Similarity	NPC173347
0.8319	Intermediate Similarity	NPC475372
0.8319	Intermediate Similarity	NPC473720
0.8306	Intermediate Similarity	NPC311534
0.8305	Intermediate Similarity	NPC148458
0.8304	Intermediate Similarity	NPC475050
0.8293	Intermediate Similarity	NPC120994
0.8293	Intermediate Similarity	NPC203702
0.8291	Intermediate Similarity	NPC25909
0.8291	Intermediate Similarity	NPC962
0.8288	Intermediate Similarity	NPC476897
0.8276	Intermediate Similarity	NPC470076
0.8276	Intermediate Similarity	NPC317107
0.8273	Intermediate Similarity	NPC316598
0.8264	Intermediate Similarity	NPC310511
0.8264	Intermediate Similarity	NPC312481
0.8261	Intermediate Similarity	NPC214644
0.8261	Intermediate Similarity	NPC87335
0.8261	Intermediate Similarity	NPC41405
0.8254	Intermediate Similarity	NPC471855
0.825	Intermediate Similarity	NPC278681
0.825	Intermediate Similarity	NPC230513
0.825	Intermediate Similarity	NPC312536
0.8246	Intermediate Similarity	NPC187435
0.8246	Intermediate Similarity	NPC67321
0.824	Intermediate Similarity	NPC221414
0.8235	Intermediate Similarity	NPC157380
0.8235	Intermediate Similarity	NPC473656
0.823	Intermediate Similarity	NPC149124
0.823	Intermediate Similarity	NPC75531
0.8226	Intermediate Similarity	NPC287903
0.8226	Intermediate Similarity	NPC42399
0.822	Intermediate Similarity	NPC238667
0.822	Intermediate Similarity	NPC474181
0.822	Intermediate Similarity	NPC216665
0.8214	Intermediate Similarity	NPC136289
0.8211	Intermediate Similarity	NPC473255
0.8205	Intermediate Similarity	NPC317687
0.8205	Intermediate Similarity	NPC207251
0.8198	Intermediate Similarity	NPC474012
0.8198	Intermediate Similarity	NPC476299
0.819	Intermediate Similarity	NPC472214
0.819	Intermediate Similarity	NPC76084
0.819	Intermediate Similarity	NPC472215
0.819	Intermediate Similarity	NPC16270
0.8182	Intermediate Similarity	NPC112936
0.8182	Intermediate Similarity	NPC253826
0.8182	Intermediate Similarity	NPC107243
0.8174	Intermediate Similarity	NPC177064
0.8174	Intermediate Similarity	NPC472217
0.8174	Intermediate Similarity	NPC472219
0.8174	Intermediate Similarity	NPC472218
0.8167	Intermediate Similarity	NPC284707
0.8167	Intermediate Similarity	NPC16701
0.8167	Intermediate Similarity	NPC113448
0.8167	Intermediate Similarity	NPC475913
0.8167	Intermediate Similarity	NPC146786
0.816	Intermediate Similarity	NPC245094
0.816	Intermediate Similarity	NPC473888
0.8158	Intermediate Similarity	NPC266570
0.8158	Intermediate Similarity	NPC60681
0.8151	Intermediate Similarity	NPC298278
0.8151	Intermediate Similarity	NPC266728

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC474370 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	204
0.1-0.2	1477
0.2-0.3	3526
0.3-0.4	2586
0.4-0.5	815
0.5-0.6	259
0.6-0.7	140
0.7-0.8	135
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9727	High Similarity	NPD7115	Discovery
0.8205	Intermediate Similarity	NPD8297	Approved
0.8174	Intermediate Similarity	NPD6899	Approved
0.8174	Intermediate Similarity	NPD6881	Approved
0.812	Intermediate Similarity	NPD6649	Approved
0.812	Intermediate Similarity	NPD6650	Approved
0.8108	Intermediate Similarity	NPD4225	Approved
0.8087	Intermediate Similarity	NPD5697	Approved
0.8034	Intermediate Similarity	NPD7102	Approved
0.8034	Intermediate Similarity	NPD7290	Approved
0.8034	Intermediate Similarity	NPD6883	Approved
0.8033	Intermediate Similarity	NPD6319	Approved
0.8	Intermediate Similarity	NPD6402	Approved
0.8	Intermediate Similarity	NPD6675	Approved
0.8	Intermediate Similarity	NPD5739	Approved
0.8	Intermediate Similarity	NPD7128	Approved
0.7966	Intermediate Similarity	NPD8130	Phase 1
0.7966	Intermediate Similarity	NPD6617	Approved
0.7966	Intermediate Similarity	NPD6869	Approved
0.7966	Intermediate Similarity	NPD6847	Approved
0.7949	Intermediate Similarity	NPD6373	Approved
0.7949	Intermediate Similarity	NPD6372	Approved
0.7949	Intermediate Similarity	NPD6014	Approved
0.7949	Intermediate Similarity	NPD6013	Approved
0.7949	Intermediate Similarity	NPD6012	Approved
0.7899	Intermediate Similarity	NPD6882	Approved
0.7895	Intermediate Similarity	NPD5211	Phase 2
0.7863	Intermediate Similarity	NPD7320	Approved
0.7863	Intermediate Similarity	NPD6011	Approved
0.7833	Intermediate Similarity	NPD4632	Approved
0.7812	Intermediate Similarity	NPD7319	Approved
0.7778	Intermediate Similarity	NPD7492	Approved
0.7778	Intermediate Similarity	NPD5701	Approved
0.7759	Intermediate Similarity	NPD5141	Approved
0.7742	Intermediate Similarity	NPD6054	Approved
0.7734	Intermediate Similarity	NPD7736	Approved
0.7731	Intermediate Similarity	NPD6371	Approved
0.7731	Intermediate Similarity	NPD4634	Approved
0.7719	Intermediate Similarity	NPD5286	Approved
0.7719	Intermediate Similarity	NPD7640	Approved
0.7719	Intermediate Similarity	NPD4696	Approved
0.7719	Intermediate Similarity	NPD7639	Approved
0.7719	Intermediate Similarity	NPD5285	Approved
0.7717	Intermediate Similarity	NPD7507	Approved
0.7717	Intermediate Similarity	NPD6616	Approved
0.7699	Intermediate Similarity	NPD6083	Phase 2
0.7699	Intermediate Similarity	NPD6084	Phase 2
0.7692	Intermediate Similarity	NPD6008	Approved
0.768	Intermediate Similarity	NPD7503	Approved
0.7658	Intermediate Similarity	NPD6399	Phase 3
0.7656	Intermediate Similarity	NPD7078	Approved
0.7647	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5785	Approved
0.7632	Intermediate Similarity	NPD7638	Approved
0.7619	Intermediate Similarity	NPD6370	Approved
0.7586	Intermediate Similarity	NPD5225	Approved
0.7586	Intermediate Similarity	NPD4633	Approved
0.7586	Intermediate Similarity	NPD5224	Approved
0.7586	Intermediate Similarity	NPD5226	Approved
0.7559	Intermediate Similarity	NPD7604	Phase 2
0.7544	Intermediate Similarity	NPD4755	Approved
0.754	Intermediate Similarity	NPD6016	Approved
0.754	Intermediate Similarity	NPD6015	Approved
0.7522	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7521	Intermediate Similarity	NPD5175	Approved
0.7521	Intermediate Similarity	NPD5174	Approved
0.7521	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD7100	Approved
0.752	Intermediate Similarity	NPD7101	Approved
0.75	Intermediate Similarity	NPD5223	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD4202	Approved
0.748	Intermediate Similarity	NPD5988	Approved
0.7479	Intermediate Similarity	NPD6412	Phase 2
0.7478	Intermediate Similarity	NPD5696	Approved
0.746	Intermediate Similarity	NPD6059	Approved
0.744	Intermediate Similarity	NPD6335	Approved
0.744	Intermediate Similarity	NPD7327	Approved
0.744	Intermediate Similarity	NPD7328	Approved
0.7438	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6274	Approved
0.7414	Intermediate Similarity	NPD4700	Approved
0.7411	Intermediate Similarity	NPD6079	Approved
0.7402	Intermediate Similarity	NPD8033	Approved
0.7402	Intermediate Similarity	NPD5983	Phase 2
0.7391	Intermediate Similarity	NPD7902	Approved
0.7385	Intermediate Similarity	NPD8293	Discontinued
0.7381	Intermediate Similarity	NPD7516	Approved
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7368	Intermediate Similarity	NPD4629	Approved
0.7368	Intermediate Similarity	NPD5210	Approved
0.736	Intermediate Similarity	NPD6317	Approved
0.7323	Intermediate Similarity	NPD8294	Approved
0.7323	Intermediate Similarity	NPD8377	Approved
0.7317	Intermediate Similarity	NPD6053	Discontinued
0.7308	Intermediate Similarity	NPD6336	Discontinued
0.7302	Intermediate Similarity	NPD6313	Approved
0.7302	Intermediate Similarity	NPD6314	Approved
0.7297	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD7748	Approved
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD7146	Approved
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7273	Intermediate Similarity	NPD4729	Approved
0.7273	Intermediate Similarity	NPD7334	Approved
0.7273	Intermediate Similarity	NPD6686	Approved
0.7273	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6409	Approved
0.7273	Intermediate Similarity	NPD7521	Approved
0.7273	Intermediate Similarity	NPD5330	Approved
0.7273	Intermediate Similarity	NPD4730	Approved
0.7266	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD8296	Approved
0.7266	Intermediate Similarity	NPD8380	Approved
0.7266	Intermediate Similarity	NPD8335	Approved
0.7266	Intermediate Similarity	NPD8379	Approved
0.7266	Intermediate Similarity	NPD8378	Approved
0.7257	Intermediate Similarity	NPD5281	Approved
0.7257	Intermediate Similarity	NPD7515	Phase 2
0.7257	Intermediate Similarity	NPD5693	Phase 1
0.7257	Intermediate Similarity	NPD5284	Approved
0.7232	Intermediate Similarity	NPD5328	Approved
0.7232	Intermediate Similarity	NPD4753	Phase 2
0.7203	Intermediate Similarity	NPD5344	Discontinued
0.719	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD5363	Approved
0.7155	Intermediate Similarity	NPD5221	Approved
0.7155	Intermediate Similarity	NPD5222	Approved
0.7155	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD5249	Phase 3
0.7154	Intermediate Similarity	NPD5251	Approved
0.7154	Intermediate Similarity	NPD5250	Approved
0.7154	Intermediate Similarity	NPD5248	Approved
0.7154	Intermediate Similarity	NPD5247	Approved
0.7143	Intermediate Similarity	NPD7632	Discontinued
0.7143	Intermediate Similarity	NPD6903	Approved
0.7132	Intermediate Similarity	NPD6909	Approved
0.7132	Intermediate Similarity	NPD8513	Phase 3
0.7132	Intermediate Similarity	NPD6908	Approved
0.7131	Intermediate Similarity	NPD5128	Approved
0.713	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7900	Approved
0.713	Intermediate Similarity	NPD6001	Approved
0.7107	Intermediate Similarity	NPD4767	Approved
0.7107	Intermediate Similarity	NPD4768	Approved
0.7105	Intermediate Similarity	NPD8034	Phase 2
0.7105	Intermediate Similarity	NPD8035	Phase 2
0.7097	Intermediate Similarity	NPD5215	Approved
0.7097	Intermediate Similarity	NPD5217	Approved
0.7097	Intermediate Similarity	NPD5216	Approved
0.7094	Intermediate Similarity	NPD5173	Approved
0.7091	Intermediate Similarity	NPD3133	Approved
0.7091	Intermediate Similarity	NPD4786	Approved
0.7091	Intermediate Similarity	NPD3666	Approved
0.7091	Intermediate Similarity	NPD3665	Phase 1
0.7083	Intermediate Similarity	NPD4754	Approved
0.708	Intermediate Similarity	NPD6080	Approved
0.708	Intermediate Similarity	NPD6673	Approved
0.708	Intermediate Similarity	NPD6904	Approved
0.7049	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD1694	Approved
0.7023	Intermediate Similarity	NPD8328	Phase 3
0.7016	Intermediate Similarity	NPD5169	Approved
0.7016	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD5135	Approved
0.7009	Intermediate Similarity	NPD4697	Phase 3
0.7008	Intermediate Similarity	NPD6868	Approved
0.7	Intermediate Similarity	NPD8515	Approved
0.7	Intermediate Similarity	NPD8516	Approved
0.7	Intermediate Similarity	NPD8517	Approved
0.6991	Remote Similarity	NPD6672	Approved
0.6991	Remote Similarity	NPD5737	Approved
0.6984	Remote Similarity	NPD8133	Approved
0.696	Remote Similarity	NPD5127	Approved
0.6957	Remote Similarity	NPD7637	Suspended
0.694	Remote Similarity	NPD6033	Approved
0.693	Remote Similarity	NPD6051	Approved
0.6923	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3667	Approved
0.6909	Remote Similarity	NPD4221	Approved
0.6909	Remote Similarity	NPD4270	Approved
0.6909	Remote Similarity	NPD4269	Approved
0.6909	Remote Similarity	NPD4223	Phase 3
0.6903	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD5329	Approved
0.6875	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5207	Approved
0.687	Remote Similarity	NPD46	Approved
0.687	Remote Similarity	NPD6698	Approved
0.6849	Remote Similarity	NPD7236	Approved
0.6846	Remote Similarity	NPD4522	Approved
0.6842	Remote Similarity	NPD5208	Approved
0.6833	Remote Similarity	NPD6648	Approved
0.6818	Remote Similarity	NPD5369	Approved
0.6814	Remote Similarity	NPD5690	Phase 2
0.6814	Remote Similarity	NPD6098	Approved
0.6814	Remote Similarity	NPD5786	Approved
0.681	Remote Similarity	NPD6050	Approved
0.681	Remote Similarity	NPD5694	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data